Tear Jerker / Adrian Mole

• The death of May Mole, Adrian's grandmother in The Wilderness Years.
• Speaking of The Wilderness Years, Adrian's breakup with Bianca Darington could also count, given that it's the first really fulfilling romantic relationship of his adult life (arguably his life, period), and the fact that she left him for his mother's second husband. Breaking down to his father on the phone and having the character in his novel attempt suicide (and later contemplate murder) really drive home how much it has affected him.
• Although he brings some of it on himself, the way that Adrian's friends and family grow weary of him and are sometimes even openly hostile and/or nasty to him as the series progresses can be a bit painful and depressing to read. Even though there's still a humorous amount of Wangst in the later books, he's also clearly got a lot of issues and spends a significant amount of time playing the role of the Chew Toy.
• Adrian's description of his appearance while undergoing chemotherapy for prostate cancer in The Prostrate Years.
• Robbie's death at the end of ''The Weapons Of Mass Destruction hits Glenn very hard. Adrian takes it badly as well, since Robbie had quite a bit in common with Adrian and they got along based on letters sent between them. This also makes Adrian question the morality of the war, which up until that point, he supported.

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